I recently bought a pair of ankle boots, my first ever pair of boots for that matter. I have extremely slender ankles and finding any boot that doesn't wobble around has been impossible, until yesterday. I walked into marshalls hoping to find one of those great sneaky buys and of course I found it. They are suede boots, originally $200 for $45, black and very low, they are the folded over kind, and also very basic, which is what I like, less detail to mess up. When I got home I was so excited! I love to wear dresses and skirts and skinny jeans. To my dismay, skinny jeans and this particular cut of boot don't match, and then straight leg as well.
I then came to ask myself: What does one where with ankle boots? I found a lot, and not just for myself.
First, did you already buy the boots, or are you looking for the perfect pair. If you are looking for the perfect pair, figure out what style clothes you often wear. It could lots of skinny jeans, flared boot cut, short skirts, knee length dresses. Once you've figure that out, consider the shape of your body vs what you wear, then you can find the perfect pair.
Okay! These are the few general styles of ankle boots out there, obviously the design, detail and patterns greatly very, but what to look for is the height of the boot, the height of the heel, the toe.
Boot #2 it's height (where is falls on your leg) is a little high. To maximize this look, you want to establish what you're willing to wear. Leggings will look great, along with any type of short clothing (mid thigh preferable) and of course skinny jeans. Full, curvy women can pull this look off very nicely.
Boot #8 + #9 these will look best with mid length skirts, cropped leggings or short skirts (honestly, short skirts will would with any boot). If you're curvy, the mid length dress might not be idea, because it has a shortening effect. Same goes for the cropped leggings.
This is an excelent look for slender legs. The high waisted skirt adds much illusion as to the length of the leg, and the high socks with the knee/slightly above the knee puff skirt give the right about of exposure.
Ultimately, you just need to try on tons and tons of boots, with many different outfits to get a sense of what will and won't look good with your style. Everyone is different :)